Fully automated peptide radiolabeling from [ 18 F]fluoride
Abstract
The biological properties of receptor-targeted peptides have made them popular diagnostic imaging and therapeutic agents. Typically, the synthesis of fluorine-18 radiolabeled receptor-targeted peptides for positron emission tomography (PET) imaging is a time consuming, complex, multi-step synthetic process that is highly variable based on the peptide. The complexity associated with the radiolabeling route and lack of robust automated protocols can hinder translation into the clinic. A fully automated batch production to radiolabel three peptides (YGGFL, cRGDyK, and Pyr-QKLGNQWAVGHLM) from fluorine-18 using the ELIXYS FLEX/CHEM® radiosynthesizer in a two-step process is described. First, the prosthetic group, 6-[18F]fluoronicotinyl-2,3,5,6-tetrafluorophenyl ester ([18F]FPy-TFP) was synthesized and subsequently attached to the peptide. The [18F]FPy-peptides were synthesized in 13–26% decay corrected yields from fluorine-18 with high molar activity 1–5 Ci μmol-1 and radiochemical purity of >99% in an overall synthesis time of 97 ± 3 minutes.
- Authors:
-
[1];
[1]
- Department of Internal Medicine, Division of Hematology and Oncology, University of California, Davis, USA
- Sofie Co., Culver City, USA
- Department of Biomedical Engineering, University of California, Davis, USA
- Publication Date:
- Research Org.:
- Univ. of California, Davis, CA (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC); National Cancer Inst.; National Inst. of Mental Health; National Inst. of Biomedical Imaging and Bioengineering
- OSTI Identifier:
- 1500134
- Alternate Identifier(s):
- OSTI ID: 1611038
- Grant/Contract Number:
- SC0008385
- Resource Type:
- Published Article
- Journal Name:
- RSC Advances
- Additional Journal Information:
- Journal Name: RSC Advances Journal Volume: 9 Journal Issue: 15; Journal ID: ISSN 2046-2069
- Publisher:
- Royal Society of Chemistry
- Country of Publication:
- United Kingdom
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; Chemistry
Citation Formats
Davis, Ryan A., Drake, Chris, Ippisch, Robin C., Moore, Melissa, and Sutcliffe, Julie L. Fully automated peptide radiolabeling from [ 18 F]fluoride. United Kingdom: N. p., 2019.
Web. doi:10.1039/C8RA10541C.
Davis, Ryan A., Drake, Chris, Ippisch, Robin C., Moore, Melissa, & Sutcliffe, Julie L. Fully automated peptide radiolabeling from [ 18 F]fluoride. United Kingdom. https://doi.org/10.1039/C8RA10541C
Davis, Ryan A., Drake, Chris, Ippisch, Robin C., Moore, Melissa, and Sutcliffe, Julie L. Fri .
"Fully automated peptide radiolabeling from [ 18 F]fluoride". United Kingdom. https://doi.org/10.1039/C8RA10541C.
@article{osti_1500134,
title = {Fully automated peptide radiolabeling from [ 18 F]fluoride},
author = {Davis, Ryan A. and Drake, Chris and Ippisch, Robin C. and Moore, Melissa and Sutcliffe, Julie L.},
abstractNote = {The biological properties of receptor-targeted peptides have made them popular diagnostic imaging and therapeutic agents. Typically, the synthesis of fluorine-18 radiolabeled receptor-targeted peptides for positron emission tomography (PET) imaging is a time consuming, complex, multi-step synthetic process that is highly variable based on the peptide. The complexity associated with the radiolabeling route and lack of robust automated protocols can hinder translation into the clinic. A fully automated batch production to radiolabel three peptides (YGGFL, cRGDyK, and Pyr-QKLGNQWAVGHLM) from fluorine-18 using the ELIXYS FLEX/CHEM® radiosynthesizer in a two-step process is described. First, the prosthetic group, 6-[18F]fluoronicotinyl-2,3,5,6-tetrafluorophenyl ester ([18F]FPy-TFP) was synthesized and subsequently attached to the peptide. The [18F]FPy-peptides were synthesized in 13–26% decay corrected yields from fluorine-18 with high molar activity 1–5 Ci μmol-1 and radiochemical purity of >99% in an overall synthesis time of 97 ± 3 minutes.},
doi = {10.1039/C8RA10541C},
journal = {RSC Advances},
number = 15,
volume = 9,
place = {United Kingdom},
year = {Fri Mar 15 00:00:00 EDT 2019},
month = {Fri Mar 15 00:00:00 EDT 2019}
}
Free Publicly Available Full Text
Publisher's Version of Record
https://doi.org/10.1039/C8RA10541C
https://doi.org/10.1039/C8RA10541C
Other availability
Search WorldCat to find libraries that may hold this journal
Cited by: 5 works
Citation information provided by
Web of Science
Web of Science
Save to My Library
You must Sign In or Create an Account in order to save documents to your library.
Works referenced in this record:
New perspectives in cell adhesion: RGD and integrins
journal, October 1987
- Ruoslahti, E.; Pierschbacher, M.
- Science, Vol. 238, Issue 4826
A Novel Facile Method of Labeling Octreotide with 18F-Fluorine
journal, February 2010
- Laverman, P.; McBride, W. J.; Sharkey, R. M.
- Journal of Nuclear Medicine, Vol. 51, Issue 3
Radiosynthesis of a new PSMA targeting ligand ([18F]FPy-DUPA-Pep)
journal, July 2011
- Malik, Noeen; Machulla, Hans-Jürgen; Solbach, Christoph
- Applied Radiation and Isotopes, Vol. 69, Issue 7
Positron Emission Tomography As an Imaging Biomarker
journal, July 2006
- Weber, Wolfgang A.
- Journal of Clinical Oncology, Vol. 24, Issue 20
Fully automated synthesis and coupling of [ 18 F]FBEM to glutathione using the iPHASE FlexLab module : Fully automated F-18 FBEM production and coupling
journal, January 2014
- Ackermann, Uwe; Plougastel, Lucie; Wichmann, Christian
- Journal of Labelled Compounds and Radiopharmaceuticals, Vol. 57, Issue 2
Defining the Role of Integrin αvβ6 in Cancer
journal, July 2009
- Bandyopadhyay, A.; Raghavan, S.
- Current Drug Targets, Vol. 10, Issue 7
Radiolabelled RGD peptides and peptidomimetics for tumour targeting
journal, January 2009
- Haubner, Roland
- Frontiers in Bioscience, Vol. Volume, Issue 14
Solid-phase synthesis and fluorine-18 radiolabeling of cycloRGDyK
journal, January 2016
- Davis, Ryan A.; Lau, Kevin; Hausner, Sven H.
- Organic & Biomolecular Chemistry, Vol. 14, Issue 37
Automated radiochemical synthesis of [18F]FBEM: A thiol reactive synthon for radiofluorination of peptides and proteins
journal, February 2011
- Kiesewetter, Dale O.; Jacobson, Orit; Lang, Lixin
- Applied Radiation and Isotopes, Vol. 69, Issue 2
A novel 2-cyanobenzothiazole-based 18 F prosthetic group for conjugation to 1,2-aminothiol-bearing targeting vectors
journal, January 2015
- Inkster, James A. H.; Colin, Didier J.; Seimbille, Yann
- Organic & Biomolecular Chemistry, Vol. 13, Issue 12
High-Throughput Approaches to the Development of Molecular Imaging Agents
journal, November 2016
- Hu, Lina Y.; Kelly, Kimberly A.; Sutcliffe, Julie L.
- Molecular Imaging and Biology, Vol. 19, Issue 2
Noninvasive Visualization of the Activated αvβ3 Integrin in Cancer Patients by Positron Emission Tomography and [18F]Galacto-RGD
journal, March 2005
- Haubner, Roland; Weber, Wolfgang A.; Beer, Ambros J.
- PLoS Medicine, Vol. 2, Issue 3
An Update of Radiolabeled Bombesin Analogs for Gastrin-Releasing Peptide Receptor Targeting
journal, April 2013
- Yu, Zilin; Ananias, Hildo J. K.; Carlucci, Giuseppe
- Current Pharmaceutical Design, Vol. 19, Issue 18
Solid Phase Peptide Synthesis. I. The Synthesis of a Tetrapeptide
journal, July 1963
- Merrifield, R. B.
- Journal of the American Chemical Society, Vol. 85, Issue 14, p. 2149-2154
A facile automated synthesis of N-succinimidyl 4-[18F]fluorobenzoate ([18F]SFB) for 18F-labeled cell-penetrating peptide as PET tracer
journal, April 2010
- Tang, Ganghua; Tang, Xiaolan; Wang, Xinlu
- Journal of Labelled Compounds and Radiopharmaceuticals, Vol. 53, Issue 8
N , N , N -Trimethyl-5-[(2,3,5,6-tetrafluorophenoxy)carbonyl]pyridin-2-aminium trifluoromethanesulfonate a precursor for the synthesis of 2,3,5,6-tetrafluorophenyl 6-[ 18 F]-fluoronicotinate
journal, April 2018
- Davis, Ryan A.; Fettinger, James C.
- Acta Crystallographica Section C Structural Chemistry, Vol. 74, Issue 5
GRPR-selective PET imaging of prostate cancer using [18F]-lanthionine-bombesin analogs
journal, May 2015
- Carlucci, G.; Kuipers, A.; Ananias, H. J. K.
- Peptides, Vol. 67
Development of 6-[ 18 F]fluoro-carbohydrate-based prosthetic groups and their conjugation to peptides via click chemistry : [18 F]fluoro-sugar prosthetic groups and their coupling with peptides
journal, December 2015
- Collet, Charlotte; Maskali, Fatiha; Clément, Alexandra
- Journal of Labelled Compounds and Radiopharmaceuticals, Vol. 59, Issue 2
Novel Method for Radiolabeling and Dimerizing Thiolated Peptides Using 18 F-Hexafluorobenzene
journal, June 2015
- Jacobson, Orit; Yan, Xuefeng; Ma, Ying
- Bioconjugate Chemistry, Vol. 26, Issue 10
Radiosynthesis and Biodistribution of Cyclic RGD Peptides Conjugated with Novel [ 18 F]Fluorinated Aldehyde-Containing Prosthetic Groups
journal, April 2008
- Glaser, Matthias; Morrison, Matthew; Solbakken, Magne
- Bioconjugate Chemistry, Vol. 19, Issue 4
Targeted In vivo Imaging of Integrin v 6 with an Improved Radiotracer and Its Relevance in a Pancreatic Tumor Model
journal, June 2009
- Hausner, S. H.; Abbey, C. K.; Bold, R. J.
- Cancer Research, Vol. 69, Issue 14
Improved synthesis of [ 18 F]FLETT via a fully automated vacuum distillation method for [ 18 F]2-fluoroethyl azide purification
journal, December 2014
- Ackermann, Uwe; Plougastel, Lucie; Goh, Yit Wooi
- Applied Radiation and Isotopes, Vol. 94
68Ga-DOTA-Tyr3-Octreotide PET in Neuroendocrine Tumors: Comparison with Somatostatin Receptor Scintigraphy and CT
journal, April 2007
- Gabriel, M.; Decristoforo, C.; Kendler, D.
- Journal of Nuclear Medicine, Vol. 48, Issue 4
18F-Labeled Galacto and PEGylated RGD Dimers for PET Imaging of αvβ3 Integrin Expression
journal, December 2009
- Liu, Shuanglong; Liu, Zhaofei; Chen, Kai
- Molecular Imaging and Biology, Vol. 12, Issue 5
A fast, simple, and reproducible automated synthesis of [18F]FPyKYNE-c(RGDyK) for αvβ3 receptor positron emission tomography imaging: Synthesis of [18F]FPyKYNE-c(RGDyK)
journal, November 2011
- Valdivia, Ana C.; Estrada, Miriam; Hadizad, Tayebeh
- Journal of Labelled Compounds and Radiopharmaceuticals, Vol. 55, Issue 2
Fast indirect fluorine-18 labeling of protein/peptide using the useful 6-fluoronicotinic acid-2,3,5,6-tetrafluorophenyl prosthetic group: A method comparable to direct fluorination
journal, February 2017
- Basuli, Falguni; Zhang, Xiang; Woodroofe, Carolyn C.
- Journal of Labelled Compounds and Radiopharmaceuticals, Vol. 60, Issue 3
High-throughput in vivo screening of targeted molecular imaging agents
journal, October 2009
- Gagnon, M. K. J.; Hausner, S. H.; Marik, J.
- Proceedings of the National Academy of Sciences, Vol. 106, Issue 42
Investigation of bombesin peptide as a targeting ligand for the gastrin releasing peptide (GRP) receptor
journal, November 2016
- Begum, Anjuman Ara; Moyle, Peter M.; Toth, Istvan
- Bioorganic & Medicinal Chemistry, Vol. 24, Issue 22
Future directions for peptide therapeutics development
journal, September 2013
- Kaspar, Allan A.; Reichert, Janice M.
- Drug Discovery Today, Vol. 18, Issue 17-18
PET tracers for somatostatin receptor imaging of neuroendocrine tumors: current status and review of the literature
journal, November 2014
- Johnbeck, Camilla Bardram; Knigge, Ulrich; Kjær, Andreas
- Future Oncology, Vol. 10, Issue 14
Rapid 18 F-radiolabeling of peptides from [ 18 F]fluoride using a single microfluidics device
journal, January 2014
- Cumming, Robin C.; Olberg, Dag Erlend; Sutcliffe, Julie L.
- RSC Adv., Vol. 4, Issue 90
Radiolabeled Peptides: Valuable Tools for the Detection and Treatment of Cancer
journal, January 2012
- Fani, M.; Maecke, H. R.; Okarvi, S. M.
- Theranostics, Vol. 2, Issue 5
The Effect of Bi-Terminal PEGylation of an Integrin v 6-Targeted 18F Peptide on Pharmacokinetics and Tumor Uptake
journal, March 2015
- Hausner, S. H.; Bauer, N.; Hu, L. Y.
- Journal of Nuclear Medicine, Vol. 56, Issue 5
Stereoisomeric Peptide Libraries and Peptidomimetics for Designing Selective Inhibitors of theαvβ3 Integrin for a New Cancer Therapy
journal, August 1997
- Haubner, Roland; Finsinger, Dirk; Kessler, Horst
- Angewandte Chemie International Edition in English, Vol. 36, Issue 1314
Integrins in cancer: biological implications and therapeutic opportunities
journal, January 2010
- Desgrosellier, Jay S.; Cheresh, David A.
- Nature Reviews Cancer, Vol. 10, Issue 1
Fluorine-18 Radiochemistry, Labeling Strategies and Synthetic Routes
journal, December 2014
- Jacobson, Orit; Kiesewetter, Dale O.; Chen, Xiaoyuan
- Bioconjugate Chemistry, Vol. 26, Issue 1
Biodistribution of the 18F-FPPRGD2 PET radiopharmaceutical in cancer patients: an atlas of SUV measurements
journal, June 2015
- Minamimoto, Ryogo; Jamali, Mehran; Barkhodari, Amir
- European Journal of Nuclear Medicine and Molecular Imaging, Vol. 42, Issue 12
Peptide therapeutics: current status and future directions
journal, January 2015
- Fosgerau, Keld; Hoffmann, Torsten
- Drug Discovery Today, Vol. 20, Issue 1
The Impact of Somatostatin Receptor–Directed PET/CT on the Management of Patients with Neuroendocrine Tumor: A Systematic Review and Meta-Analysis
journal, January 2017
- Barrio, Martin; Czernin, Johannes; Fanti, Stefano
- Journal of Nuclear Medicine, Vol. 58, Issue 5
Understanding temperatures and pressures during short radiochemical reactions
journal, February 2016
- Lazari, Mark; Irribarren, Jonathan; Zhang, Shuang
- Applied Radiation and Isotopes, Vol. 108
Recent progress in fluorine-18 labelled peptide radiopharmaceuticals
journal, April 2001
- Okarvi, S.
- European Journal of Nuclear Medicine, Vol. 28, Issue 7
Synthesis and characterization of a high-affinity v 6-specific ligand for in vitro and in vivo applications
journal, May 2009
- Li, S.; McGuire, M. J.; Lin, M.
- Molecular Cancer Therapeutics, Vol. 8, Issue 5
Prospective of 68 Ga-Radiopharmaceutical Development
journal, January 2014
- Velikyan, Irina
- Theranostics, Vol. 4, Issue 1
Labeling Strategies of Peptides with 18F for Positron Emission Tomography
journal, November 2010
- E. Olberg, D.; K. Hjelstuen, O.
- Current Topics in Medicinal Chemistry, Vol. 10, Issue 16
18F-Fluorobenzoate-Labeled Cystine Knot Peptides for PET Imaging of Integrin v 6
journal, May 2013
- Hackel, B. J.; Kimura, R. H.; Miao, Z.
- Journal of Nuclear Medicine, Vol. 54, Issue 7
One Step Radiosynthesis of 6-[ 18 F]Fluoronicotinic Acid 2,3,5,6-Tetrafluorophenyl Ester ([ 18 F]F-Py-TFP): A New Prosthetic Group for Efficient Labeling of Biomolecules with Fluorine-18
journal, February 2010
- Olberg, Dag E.; Arukwe, Joseph M.; Grace, David
- Journal of Medicinal Chemistry, Vol. 53, Issue 4
Facile room temperature synthesis of fluorine-18 labeled fluoronicotinic acid-2,3,5,6-tetrafluorophenyl ester without azeotropic drying of fluorine-18
journal, December 2016
- Basuli, Falguni; Zhang, Xiang; Jagoda, Elaine M.
- Nuclear Medicine and Biology, Vol. 43, Issue 12
18F-Labeled Peptides: The Future Is Bright
journal, December 2014
- Richter, Susan; Wuest, Frank
- Molecules, Vol. 19, Issue 12
Production of diverse PET probes with limited resources: 24 18 F-labeled compounds prepared with a single radiosynthesizer
journal, October 2017
- Collins, Jeffrey; Waldmann, Christopher M.; Drake, Christopher
- Proceedings of the National Academy of Sciences, Vol. 114, Issue 43
[ 18 F]Galacto-RGD: Synthesis, Radiolabeling, Metabolic Stability, and Radiation Dose Estimates
journal, January 2004
- Haubner, Roland; Kuhnast, Bertrand; Mang, Christian
- Bioconjugate Chemistry, Vol. 15, Issue 1
RGD-Based Strategies To Target Alpha(v) Beta(3) Integrin in Cancer Therapy and Diagnosis
journal, October 2012
- Danhier, Fabienne; Le Breton, Aude; Préat, Véronique
- Molecular Pharmaceutics, Vol. 9, Issue 11
Phase I Trial of the Positron-Emitting Arg-Gly-Asp (RGD) Peptide Radioligand 18F-AH111585 in Breast Cancer Patients
journal, May 2008
- Kenny, L. M.; Coombes, R. C.; Oulie, I.
- Journal of Nuclear Medicine, Vol. 49, Issue 6
Strain-Promoted Copper-Free “Click” Chemistry for 18F Radiolabeling of Bombesin
journal, September 2011
- Campbell-Verduyn, Lachlan S.; Mirfeizi, Leila; Schoonen, Anne K.
- Angewandte Chemie International Edition, Vol. 50, Issue 47
Radiolabelled RGD peptides for imaging and therapy
journal, February 2012
- Gaertner, F. C.; Kessler, H.; Wester, H. -J.
- European Journal of Nuclear Medicine and Molecular Imaging, Vol. 39, Issue S1
Preclinical Development and First-in-Human Imaging of the Integrin α v β 6 with [ 18 F]α v β 6 -Binding Peptide in Metastatic Carcinoma
journal, November 2018
- Hausner, Sven H.; Bold, Richard J.; Cheuy, Lina Y.
- Clinical Cancer Research, Vol. 25, Issue 4
Fully Automated Preparation and Conjugation of N-Succinimidyl 4-[18F]Fluorobenzoate ([18F]SFB) with RGD Peptide Using a GE FASTlab™ Synthesizer
journal, January 2011
- Thonon, David; Goblet, David; Goukens, Eve
- Molecular Imaging and Biology, Vol. 13, Issue 6